1512-30-7

Basic information

• Product Name: difluoromethanesulphonyl chloride
• Synonyms: difluoromethanesulphonyl chloride;Difluoromethanesulfonic acid chloride;Methanesulfonylchloride, 1,1-difluoro-
• CAS NO: 1512-30-7
• Molecular Formula: CHClF₂O₂S
• Molecular Weight: 150.5322464
• EINECS: 216-150-7
• Mol File: 1512-30-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 84.7°Cat760mmHg
• Flash Point: 5℃
• Appearance: /
• Density: 1.696g/cm³
• Vapor Pressure: 79.9mmHg at 25°C
• Refractive Index: 1.379
• CAS DataBase Reference: difluoromethanesulphonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: difluoromethanesulphonyl chloride(1512-30-7)
• EPA Substance Registry System: difluoromethanesulphonyl chloride(1512-30-7)

Safety Data

• Statements: 34
• Safety Statements: 36
• RIDADR: UN 2924 8(3) / PGII
• WGK Germany: 3
• Hazardous Substances Data: 1512-30-7(Hazardous Substances Data)

Usage

Uses

Difluoromethanesulfonyl Chloride is a reactant used in the synthesis of ketoconazole sulfonamide analogs as antifungal agents.

InChI:InChI=1/CHClF2O2S/c2-7(5,6)1(3)4/h1H

Synthetic route

[(difluoromethyl)thio]methylbenzene (68965-44-6) → difluoromethylsulfonyl chloride (1512-30-7)

Conditions	Yield
With water; chlorine at -5 - 10℃; for 3h;	82%
With water; chlorine at -10℃; Inert atmosphere;	72%
With chlorine In water at -10℃;	72%

difluoromethanesulfonic acid (40856-07-3) → difluoromethylsulfonyl chloride (1512-30-7)

Conditions	Yield
With phosphorus pentachloride

difluoromethylsulfonyl chloride (1512-30-7) + acrylonitrile (107-13-1) → 4,4-difluorobutanenitrile

Conditions	Yield
With tris-(trimethylsilyl)silane; tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20℃; Michael Addition; Inert atmosphere; Sealed tube; Irradiation;	100%

4-Phenyl-1-butene (768-56-9) + difluoromethylsulfonyl chloride (1512-30-7) → (3-chloro-5,5-difluoropentyl)benzene

Conditions	Yield
With dilauryl peroxide In dichloromethane at 70℃; for 8h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	99%

difluoromethylsulfonyl chloride (1512-30-7) + N-(4-acetylphenyl)-2-propenamide (22535-53-1) → N-(4-acetylphenyl)-2-chloro-4,4-difluorobutanamide

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	98%

difluoromethylsulfonyl chloride (1512-30-7) + p-nitrophenyl acrylate (2123-85-5) → 4-nitrophenyl 2-chloro-4,4-difluorobutanoate

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	98%

difluoromethylsulfonyl chloride (1512-30-7) + C16H13NO2 → methyl 6-(difluoromethyl)-8-methylphenanthridine-3-carboxylate

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); sodium carbonate In 1,4-dioxane; water at 20℃; for 18h; Inert atmosphere; Sealed tube; Photolysis;	98%

difluoromethylsulfonyl chloride (1512-30-7) + C18H22O6 → 1,1-diethyl 3-methyl 3-(2,2-difluoroethyl)-2,3-dihydro-1H-indene-1,1,3-tricarboxylate

Conditions	Yield
With disodium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III) In acetonitrile at 20 - 55℃; for 18h; Inert atmosphere; Sealed tube; Irradiation;	98%

difluoromethylsulfonyl chloride (1512-30-7) + N-(4-cyanophenyl)prop-2-enamide (90842-07-2) → 2-chloro-N-(4-cyanophenyl)-4,4-difluorobutanamide

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	96%

difluoromethylsulfonyl chloride (1512-30-7) + N-(4-methoxyphenyl)acrylamide (7766-37-2) → 2-chloro-4,4-difluoro-N-(4-methoxyphenyl)butanamide

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	95%

1-(2,3-dihydroindol-1-yl)propenone (104902-94-5) + difluoromethylsulfonyl chloride (1512-30-7) → 2-chloro-4,4-difluoro-1-(indolin-1-yl)butan-1-one

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	95%

difluoromethylsulfonyl chloride (1512-30-7) + 3-phenylpropyl acrylate (85909-41-7) → 3-phenylpropyl 4,4-difluorobutanoate

Conditions	Yield
With tris-(trimethylsilyl)silane; tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20℃; Michael Addition; Inert atmosphere; Sealed tube; Irradiation;	95%

N-acryloylaniline (2210-24-4) + difluoromethylsulfonyl chloride (1512-30-7) → 2-chloro-4,4-difluoro-N-phenylbutanamide

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	94%

N-methyl-N-phenylacrylamide (6273-94-5) + difluoromethylsulfonyl chloride (1512-30-7) → 2-chloro-4,4-difluoro-N-methyl-N-phenylbutanamide

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	94%

2-isocyano-4’-methoxy-5-methyl-1,1’-biphenyl (1428264-91-8) + difluoromethylsulfonyl chloride (1512-30-7) → 6-(difluoromethyl)-8-methoxy-2-methylphenanthridine

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); sodium carbonate In 1,4-dioxane; water at 20℃; for 18h; Inert atmosphere; Sealed tube; Photolysis;	93%

difluoromethylsulfonyl chloride (1512-30-7) + N-(4-(benzyloxy)-3,5-dimethylbenzyl)-N-tert-butylmethacrylamide → 2-tert-butyl-4-(2,2-difluoroethyl)-4,7,9-trimethyl-2-azaspiro[4.5]deca-6,9-diene-3,8-dione

Conditions	Yield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III) In water; acetonitrile at 20℃; for 18h; Inert atmosphere; Sealed tube; Irradiation;	93%

phenyl acrylate (937-41-7) + difluoromethylsulfonyl chloride (1512-30-7) → C10H9ClF2O2

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	92%

difluoromethylsulfonyl chloride (1512-30-7) + Phenyl vinyl ketone (768-03-6) → 2-chloro-4,4-difluoro-1-phenylbutan-1-one

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	92%

PVS (5535-48-8) + difluoromethylsulfonyl chloride (1512-30-7) → ((1-chloro-3,3-difluoropropyl)sulfonyl)benzene

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	92%

difluoromethylsulfonyl chloride (1512-30-7) + 2-isocyano-4’,5-dimethyl-1,1’-biphenyl → 6-(difluoromethyl)-2,8-dimethylphenanthridine

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); sodium carbonate In 1,4-dioxane; water at 20℃; for 18h; Inert atmosphere; Sealed tube; Photolysis;	92%

phenyl acrylate (937-41-7) + difluoromethylsulfonyl chloride (1512-30-7) → phenyl 4,4-difluorobutanoate

Conditions	Yield
With tris-(trimethylsilyl)silane; tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20℃; Michael Addition; Inert atmosphere; Sealed tube; Irradiation;	92%

PVS (5535-48-8) + difluoromethylsulfonyl chloride (1512-30-7) → ((3,3-difluoropropyl)sulfonyl)benzene

Conditions	Yield
With tris-(trimethylsilyl)silane; tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20℃; Michael Addition; Inert atmosphere; Sealed tube; Irradiation;	92%

2-phenylacrylic acid (492-38-6) + difluoromethylsulfonyl chloride (1512-30-7) → 2-chloro-4,4-difluoro-2-phenylbutanoic acid

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	91%

oct-1-ene (111-66-0) + difluoromethylsulfonyl chloride (1512-30-7) → 3-chloro-1,1-difluorononane

Conditions	Yield
With dilauryl peroxide In dichloromethane at 70℃; for 8h; Inert atmosphere;	90%

allylbenzene (300-57-2) + difluoromethylsulfonyl chloride (1512-30-7) → (2-chloro-4,4-difluorobutyl)benzene

Conditions	Yield
With dilauryl peroxide In dichloromethane at 70℃; for 8h; Inert atmosphere;	90%

vinyl benzoate (583-04-0) + difluoromethylsulfonyl chloride (1512-30-7) → 2-chloro-4,4-difluorobutyl benzoate

Conditions	Yield
With dilauryl peroxide In dichloromethane at 70℃; for 8h; Inert atmosphere;	90%

difluoromethylsulfonyl chloride (1512-30-7) + N-benzylacrylamide (13304-62-6) → N-benzyl-2-chloro-4,4-difluorobutanamide

Conditions	Yield
With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 100℃; Sealed tube; Inert atmosphere; Irradiation;	90%

difluoromethylsulfonyl chloride (1512-30-7) + N-((1-allylcyclohexyl)methyl)-4-methylbenzenesulfonamide (81097-22-5) → 3-(2,2-difluoroethyl)-2-tosyl-2-azaspiro[4.5]decane

Conditions	Yield
With [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl; silver carbonate In 1,2-dichloro-ethane at 75℃; for 18h; Inert atmosphere; Sealed tube; Irradiation;	90%

difluoromethylsulfonyl chloride (1512-30-7) + methyl 1-allylcyclohexane-1-carboxylate (67838-02-2) → 3-(2,2-difluoroethyl)-2-oxaspiro[4.5]decan-1-one

Conditions	Yield
With [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl; silver carbonate In 1,2-dichloro-ethane at 75℃; for 18h; Inert atmosphere; Sealed tube; Irradiation;	90%

2-methyl-1H-indole (95-20-5) + difluoromethylsulfonyl chloride (1512-30-7) → 3-((difluoromethyl)thio)-2-methyl-1H-indole

Conditions	Yield
With phosphonic acid diethyl ester In acetonitrile at 90℃; for 7h;	90%

difluoromethylsulfonyl chloride (1512-30-7) + dimethylbiguanide (657-24-9) → N-(difluoromethanesulfonyl)metformin

Conditions	Yield
With potassium hydroxide In acetone at 20℃;	90%
With potassium hydroxide In acetonitrile at 20℃; Inert atmosphere;	83%

5-methoxylindole (1006-94-6) + difluoromethylsulfonyl chloride (1512-30-7) → 3-((difluoromethyl)thio)-5-methoxy-1H-indole

Conditions	Yield
With phosphonic acid diethyl ester In acetonitrile at 90℃; for 7h;	89%

Upstream product

• 68965-44-6 [(difluoromethyl)thio]methylbenzene 
• 40856-07-3 difluoromethanesulfonic acid 

Downstream Products

• 37931-10-5 3-Phenylthio-difluormethan-sulfonanilid 
• 50585-74-5 difluoromethanesulfonamide 
• 658-43-5 difluoromethanesulfonanilide 
• 1554-47-8 difluoromethanesulfonyl fluoride 
• 1493-03-4 iododifluoromethane 

Relevant articles and documents

Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones

A visible light-mediated difluoromethylation of N-benzylacrylamides with HCF2SO2Cl as the HCF2 radical precursor is described. The reaction incorporates a tandem cyclization/dearomatization process to afford various difluoromethylated 2-azaspiro[4.5]deca-6,9-diene-3,8-diones bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields.

Photoredox-Catalyzed Tandem Insertion/Cyclization Reactions of Difluoromethyl and 1,1-Difluoroalkyl Radicals with Biphenyl Isocyanides

Using visible-light photoredox conditions, difluoromethylation and 1,1-difluoroalkylation of biphenyl isocyanides have allowed the synthesis of a series of 6-(difluoromethyl)- and 6-(1,1-difluoroalkyl)phenanthridines via tandem addition/cyclization/oxidation processes. The reactions are carried out in wet dioxane at room temperature using fac-Ir(ppy)3 as catalyst to form a large variety of substituted phenanthridine products in good to excellent yield.

Photoredox-catalyzed tandem radical cyclization of N-arylacrylamides: General methods to construct fluorinated 3,3-disubstituted 2-oxindoles using fluoroalkylsulfonyl chlorides

Fluorinated radicals were generated from RfSO2Cl by photoredox catalysis under mild conditions, where Rf = n-C4F9, CF3, CF2H, CH2F, CH2CF3, and CF2CO2Me. This method provided a general way to construct fluorinated 2-oxindoles from reaction with N-arylacrylamides via a proposed tandem radical cyclization process.